Ammonium Chloride → HCID 10080968, compound

Temperature

-10 °C

A suspension of 4.35 g (12.2 mmol) of triphenylmethylphosphonium bromide in 30 ml of tetrahydrofuran was cooled to -10° C. and 12.1 mmol of a 1.44M solution of butyllithium were dropwise added thereto over a period of 5 minutes. After the resulting mixture was stirred at 0° C. for 40 minutes, a solution of 1.99 g (11.0 mmol) of 3-methoxy-2-nitrobenzaldehyde in 10 ml of tetrahydrofuran was dropwise added thereto over a period of 10 minutes. The temperature of the reaction mixture was allowed to rise to room temperature. After stirring for 16 hours, the reaction mixture was poured into an aqueous solution of ammonium chloride followed by extracting with ether. The ethereal extract was washed with a saturated aqueous solution of sodium chloride and the solvent was distilled off. The residue was purified by column chromatography through 100 g of silica gel using a 15-20:100 mixture of ethyl acetate and hexane as an eluent to give 1.50 g (76%) of the title compound.

1. waitover a period of 10 minutes
2. customto rise to room temperature
3. stirringAfter stirring for 16 hours
4. extractionby extracting with ether
5. extractionThe ethereal extract
6. washwas washed with a saturated aqueous solution of sodium chloride
7. distillationthe solvent was distilled off
8. customThe residue was purified by column chromatography through 100 g of silica gel using
9. additiona 15-20:100 mixture of ethyl acetate and hexane as an eluent

ORD record

ord-1203c9a036604c3580a840c4981c9ae1

Source dataset

uspto-grants-1996_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05563169